Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 71, Issue 20, Pages 7800-7804Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo061352c
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- NIDA NIH HHS [DA07215] Funding Source: Medline
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[GRAPHICS] The preparation of C3 oxaza adamantyl cannabinoids has been described starting from phloroglucinol. Straightforward manipulations of the aromatic ring lead to a bromononaflate that is a benzyne precursor and that serves as a common intermediate for the synthesis of diverse C3-substituted tricyclic cannabinoids. Generation of the benzyne in the presence of an oxaza adamantyl amide anion results in efficient and regiospecific addition to C3 of the aromatic ring. This represents an attractive strategy for the synthesis of classical tricyclic cannabinoids that bear a modified aromatic appendage. The oxaza adamantyl cannabinoids that have been prepared represent a new class of ligands for the CB1 and CB2 receptors.
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